Jiraiya x Reader Stories(Smut)

As Time Goes By

Reader request! Reader is a shinobi who is under cover in a small village as a singer and Jiraiya was sent to check on her. They hit it off and things go slightly awry.
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Oh sure!

Hey Jiraiya! Go walk into the lion's den and seek out the undercover spy we have stationed there and get a report from her! No biggie! It shouldn't be a problem for you. Even though we got reports of these thugs killing some of our ninja and throwing parts of their bodies at the border who accidentally passed through in uniform... You should be fine though!

Jiraiya sighed loudly with obvious annoyance. Yeah he understood why it was so vague. If the message got intercepted and description of the spy set in the town was put down, her cover would be blown. Her months of work for nothing! What's worse is that she'd be in danger without realizing it and it would be too late to get her out. But still! Annoying! He's kinda just gotta wander into a hostile town that doesn't take kindly to shinobi and step carefully with every action. The only real benefit he sees is that the spy in question was working in a cabaret. It meant drinking and at least a good show. With plenty of scantly clad women for him to stare at as they bring him his drinks. Just because he's on a mission doesn't mean he can't have fun.

The moment he stepped foot in town he was met with what he about expected. At the gate that welcomed people into town, Jiraiya was stopped by a rough looking man that patted him down for weapons while another searched his bag.

"And what business do you have on our turf?" One of the guards asked.

"Oh nothing much." Jiraiya replies casually. He's feigning ignorance about their hostility and brashness. If he's argumentative, they'll be suspicious. It's best to just slide on by as peacefully as possible. "Just passing through. Anything to do for entertainment around here?"

The punk holding his pack spoke next. "We got a bar with singing and dancing and stuff downtown." A pervy grin grows on the younger man's face. "There's this one chick... her voice... her body!"

The other guard hit his comrade. "Dude that's the boss' gal! You don't go talking like that." He turned to Jiraiya and bid him farewell with a warning. "And you! Don't start no trouble. We won't hesitate to..." He drew a line across his neck in the iconic gesture.

"Gotcha." Jiraiya said flatly. It's like being intimated by a vaudeville act. All that's missing is the jaunty music and over the top sound effects. These two don't seem so clever. But they are entertaining. Maybe they should work for the cabaret with this little number. He grabbed his stuff and moved on.

It wasn't so hard to find the cabaret. There was only a few bars in town and this one had the most traffic. The best place to start looking is where the most activity is. If you are as good as they say, you'll be either very easy to find or very hard. Plus, he's very interested in "the boss' gal" the goon talked about. She must be really something if the boss of this little rinky dink town was into her.

From what Jiraiya has gathered so far, there was some kind of take over. That much was obvious to most of the people in this corner of the land. They were all on edge and worrying about their own land. It seems a group of brigands overran and overtook the current social hierarchy. He got the five second version in the corespondents. Honestly he's walking in almost completely blind.

It was a large and short tempered group that wanted a place to call their own. They took this place and have been terrorizing the people ever since. There was rules and regulations. They killed anyone who was out it line. Their leader was a brute, but smart. He didn't trust anyone and had guards at night to protect him. Hence why the need for a mole. Your mission was to get close to the leader and assassinate him when the opportunity showed itself. But it was taking longer than expected and Jiraiya was now officially your kinda sorta reliable backup. If your assessment of the situation seemed bleak or if you were too into your cover, he's there to pull you out or assist.